Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers
ABSTRACT Crosslinked organic semiconductors have opened the way for various fabrication techniques in the field of organic electronics owing to their three‐dimensional network structure with high solvent resistivity. However, recent efforts to synthesize cross‐linkable semiconducting polymers have b...
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Wiley
2025-01-01
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| Online Access: | https://doi.org/10.1002/eom2.12513 |
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| author | Jaehoon Lee Seungju Kang Eunsoo Lee Jiyun Lee Tae Woong Yoon Min‐Jae Kim Yongjoon Cho Mingfei Xiao Yorrick Boeije Wenjin Zhu Changduk Yang Jin‐Wook Lee Sungjoo Lee Guobing Zhang Henning Sirringhaus Boseok Kang |
| author_facet | Jaehoon Lee Seungju Kang Eunsoo Lee Jiyun Lee Tae Woong Yoon Min‐Jae Kim Yongjoon Cho Mingfei Xiao Yorrick Boeije Wenjin Zhu Changduk Yang Jin‐Wook Lee Sungjoo Lee Guobing Zhang Henning Sirringhaus Boseok Kang |
| author_sort | Jaehoon Lee |
| collection | DOAJ |
| description | ABSTRACT Crosslinked organic semiconductors have opened the way for various fabrication techniques in the field of organic electronics owing to their three‐dimensional network structure with high solvent resistivity. However, recent efforts to synthesize cross‐linkable semiconducting polymers have been limited by their low molecular weights and yields. In this study, this limitation is overcome by a novel post‐polymerization strategy. A reagent with a cross‐linkable functional group, (3‐mercaptopropyl)trimethoxysilane, is attached to a diketopyrrolopyrrole‐based donor–acceptor copolymer (DPPTT) via thioesterification and para‐fluoro‐thiol reaction, modifying two sites simultaneously. This modification preserves the molecular weight and electrical properties of the original polymers. In addition, the use of click chemistry enables high yield (98%) without any purification. The modified DPPTT demonstrated high resistance to organic solvents (80% retention dipped in 1‐chlorobenzene for 1 h). Exploiting this benefit, an ultrathin flexible array of 100 organic field‐effect transistors fabricated using conventional photolithography showed high‐performance reliability. Thus, this study provides a universal strategy to synthesize versatile polymer semiconductors for practical organic electronics. |
| format | Article |
| id | doaj-art-9ee127a705e84e1587049cfcb0cc32db |
| institution | Kabale University |
| issn | 2567-3173 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | EcoMat |
| spelling | doaj-art-9ee127a705e84e1587049cfcb0cc32db2025-01-16T00:02:33ZengWileyEcoMat2567-31732025-01-0171n/an/a10.1002/eom2.12513Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting PolymersJaehoon Lee0Seungju Kang1Eunsoo Lee2Jiyun Lee3Tae Woong Yoon4Min‐Jae Kim5Yongjoon Cho6Mingfei Xiao7Yorrick Boeije8Wenjin Zhu9Changduk Yang10Jin‐Wook Lee11Sungjoo Lee12Guobing Zhang13Henning Sirringhaus14Boseok Kang15SKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSchool of Energy and Chemical Engineering, Perovtronics Research Center, Low Dimensional Carbon Materials Center Ulsan National Institute of Science and Technology (UNIST) Ulsan South KoreaDepartment of Instrument Science and Technology, School of Mechanical Science and Engineering Huazhong University of Science and Technology Wuhan ChinaDepartment of Physics, Cavendish Laboratory University of Cambridge Cambridge UKOptoelectronics Group, Cavendish Laboratory University of Cambridge Cambridge UKSchool of Energy and Chemical Engineering, Perovtronics Research Center, Low Dimensional Carbon Materials Center Ulsan National Institute of Science and Technology (UNIST) Ulsan South KoreaSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaSpecial Display and Imaging Technology Innovation Center of Anhui Province, State Key Laboratory of Advanced Display Technology, Academy of Opto‐Electronic Technology Hefei University of Technology Hefei P. R. ChinaOptoelectronics Group, Cavendish Laboratory University of Cambridge Cambridge UKSKKU Advanced Institute of Nanotechnology (SAINT) and Department of Nano Science and Technology Sungkyunkwan University Suwon KoreaABSTRACT Crosslinked organic semiconductors have opened the way for various fabrication techniques in the field of organic electronics owing to their three‐dimensional network structure with high solvent resistivity. However, recent efforts to synthesize cross‐linkable semiconducting polymers have been limited by their low molecular weights and yields. In this study, this limitation is overcome by a novel post‐polymerization strategy. A reagent with a cross‐linkable functional group, (3‐mercaptopropyl)trimethoxysilane, is attached to a diketopyrrolopyrrole‐based donor–acceptor copolymer (DPPTT) via thioesterification and para‐fluoro‐thiol reaction, modifying two sites simultaneously. This modification preserves the molecular weight and electrical properties of the original polymers. In addition, the use of click chemistry enables high yield (98%) without any purification. The modified DPPTT demonstrated high resistance to organic solvents (80% retention dipped in 1‐chlorobenzene for 1 h). Exploiting this benefit, an ultrathin flexible array of 100 organic field‐effect transistors fabricated using conventional photolithography showed high‐performance reliability. Thus, this study provides a universal strategy to synthesize versatile polymer semiconductors for practical organic electronics.https://doi.org/10.1002/eom2.12513click chemistrycrosslinkingorganic semiconductorpost‐polymerization chemistrysolvent resistancetransistor array |
| spellingShingle | Jaehoon Lee Seungju Kang Eunsoo Lee Jiyun Lee Tae Woong Yoon Min‐Jae Kim Yongjoon Cho Mingfei Xiao Yorrick Boeije Wenjin Zhu Changduk Yang Jin‐Wook Lee Sungjoo Lee Guobing Zhang Henning Sirringhaus Boseok Kang Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers EcoMat click chemistry crosslinking organic semiconductor post‐polymerization chemistry solvent resistance transistor array |
| title | Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers |
| title_full | Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers |
| title_fullStr | Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers |
| title_full_unstemmed | Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers |
| title_short | Post‐Polymerization Strategy via Dual Site Clicking for Synthesizing Intrinsically Cross‐Linkable Semiconducting Polymers |
| title_sort | post polymerization strategy via dual site clicking for synthesizing intrinsically cross linkable semiconducting polymers |
| topic | click chemistry crosslinking organic semiconductor post‐polymerization chemistry solvent resistance transistor array |
| url | https://doi.org/10.1002/eom2.12513 |
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